91718-20-6Relevant articles and documents
Pd-Catalyzed ipso, meta-Dimethylation of ortho-Substituted Iodoarenes via a Base-Controlled C-H Activation Cascade with Dimethyl Carbonate as the Methyl Source
Wu, Zhuo,Wei, Feng,Wan, Bin,Zhang, Yanghui
, p. 4524 - 4530 (2021/05/04)
A methyl group can have a profound impact on the pharmacological properties of organic molecules. Hence, developing methylation methods and methylating reagents is essential in medicinal chemistry. We report a palladium-catalyzed dimethylation reaction of ortho-substituted iodoarenes using dimethyl carbonate as a methyl source. In the presence of K2CO3 as a base, iodoarenes are dimethylated at the ipso- and meta-positions of the iodo group, which represents a novel strategy for meta-C-H methylation. With KOAc as the base, subsequent oxidative C(sp3)-H/C(sp3)-H coupling occurs; in this case, the overall transformation achieves triple C-H activation to form three new C-C bonds. These reactions allow expedient access to 2,6-dimethylated phenols, 2,3-dihydrobenzofurans, and indanes, which are ubiquitous structural motifs and essential synthetic intermediates of biologically and pharmacologically active compounds.
Protecting Group-Controlled Remote Regioselective Electrophilic Aromatic Halogenation Reactions
Brittain, William D. G.,Cobb, Steven L.
, p. 6862 - 6871 (2020/07/07)
Being able to utilize a protecting group to influence remote regiocontrol offers a simple alternative approach to direct late-stage functionalization of complex organic molecules. However, protecting groups that have the ability to influence reaction regi
COMPOUND
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Page/Page column 135, (2008/06/13)
There is provided a compound of Formula (I):wherein R3, R4, R5, R6, R7, R9, and R10, are independently selected from -H, -OH, hydrocarbyl groups, oxyhydrocarbyl groups, cyano (-CN), nitro (-NO2 ), and halogens; wherein ring A is optionally further substituted wherein X is a bond or a linker group wherein (A) (i) R9 is selected from alkyl and halogen groups; and (ii) R10 is selected from -OH, oxyhydrocarbyl and -OSO 2 NR1 R2 ; wherein R1 and R2 are independently selected from H and hydrocarbyl or (B) at least one of R3 , R4 , R5 , R6 and R7 is the group -C(=0)-CR11 R12 -R8 wherein R8 is a selected from (i) an alkyloxyalkyl group (ii) a nitrile group, (iii) alkylaryl group, wherein the aryl group is substituted by other than a C1-10 group (iv) alkenylaryl group wherein the aryl group is substituted (v) alkylheteroaryl group, wherein when heteroaryl group comprises only C and N in the ring, the aryl group is substituted by other than a methyl group (vi) alkenylheteroaryl group (vii) =N-O-alkyl or =N-O-H group (viii) branched alkenyl (ix) alkyl-alcohol group or alkenyl-alcohol group (x) amide or alkylamide wherein (a) the alkyl of the alkylamide is -CH 2 - or - CH 2 CH 2 -, (b) the amide is di-substituted and/or (c) the amide is substituted with at least one of alkylheterocycle group, alkenylheterocycle group, alkylheteroaryl group, alkenylheteroaryl group, heteroaryl group, alkylamine group, alkyloxyalkyl group, alkylaryl group, straight or branched alkyl group, (xi)-CHO, or together with another of R3 , R4 , R5 , R6 and R7 the enol tautomer thereof wherein R11 and R12 are independently selected from H and hydrocarbyl; or (C) at least one of R3 , R4 , R5 , R6 and R7 together with another of R3 , R4 , R5 , R6 and R7 forms a ring containing -C(=O)-; or (D) at least one of R3 , R4 , R5 , R6 and R7 is selected from alkylheterocycle group, alkenylheterocycle group, alkylheteroaryl group, alkenylheteroaryl group, and heteroaryl groups or (E) at least one of R3 , R4 , R5 , R6 and R7 is selected from -CN, -C(R13 )=N-O-alkyl group, - C(R14 )=N-O-H group, optionally substituted pyrazole, optionally substituted thiazole, optionally substituted oxazole, optionally substituted isoxazole, optionally substituted pyridine, and optionally substituted pyrimidine, or together with another of R3 , R4 , R5 , R6 and R7 forms a nitrogen containing ring; wherein R13 and R14 are independently selected from H and hydrocarbyl